Every Ben Affleck Movie Ranked From Worst To Best

Kevin Smith's most mature film to date - and surely ever - is damn-near his best. Chasing Amy is an irreverent romantic dramedy about comic book artist Holden McNeil (Affleck) and his romantic entanglement with a lesbian woman, Alyssa (Joey Lauren Adams).

Chasing Amy feels like a much trickier film to discuss now than it did upon release, where it was heralded as an ahead-of-its-time commentary on the fluidity of human sexuality.

Today some of the film's more on-the-nose remarks might feel a little dated, but its sheer charm remains firmly in tact, in large part thanks to the performances of Affleck, Adams, and Jason Lee.

As much as folks love to rag on Smith's filmmaking, this is the closest he's ever gotten to making a "proper" dramatic movie.